First. Chose a period that you like.
My design aesthetic - if I could chose any style under the sun to wear - is the 1930s, 1940s, and 1950s (primarily 1950s). Maybe I'm infatuated with the 1950s because I grew up in the 80s when lots of clothes were fashioned after the 50s. (Yes the 80s were the age of Flashdance and torn sweatshirts and leg warmers. No I didn't wear that style - it was banned at the high school I went to and it wasn't appropriate for the Real Estate Office I worked in as receptionist.)
$44.99 1950s Inspired Dress from ModCloth
Second. Learn more about that period's clothing style by looking at vintage patterns, online clothing stores, or fashion history sites.
There are lots of stores out there that have vintage patterns or clothes for sale. SoVintagePatterns is a good place to start for women. They group patterns by period - 1940s, 1950s, etc. This is great if you like a particular style but aren't sure what period it's actually from. RustyZipper is a good place to start for men. They group suits by period - 1940s & 50s, 1960s, etc. Fashion-Era.com walks you through what happened in a period to influence changes in fashion. Information is grouped by period.
For example, I love this 1930s outfit that Nicole Kidman wore in Australia. It won't work for our 1950s shoot. But I love it anyway.:
While it's not appropriate for a 1950s shoot, I was able to find a skirt type from the 50s that had a similar silhouette - Slim Mermaid Skirts.
Third. Consider your theme for period accessories.
As you know we're going to be doing a vintage photo shoot that focuses on cooking (it's for the cover of our cookbook we'll be giving out as a wedding favor). SoVintagePatterns has a wide range of Vintage Apron Patterns.
Fourth. Select your location.
Once you have your clothes figured out, you need to take a look around the room or space you'll be photographed in. If you're looking to get photographed in a kitchen, you probably don't want a granite countertops with stainless steel appliances. Antique Vintage Appliances offers kitchen appliances so you can get a general idea of what 1950s appliances looked like.
If you don't want to transform a space for an afternoon, check out local restaurants. In San Francisco, there are a few 1950s-styled diners. For example, It's Tops.
(Source: Photograph by Jimmy L)
Fifth. Outfit your location.
If the decor and knick knacks in the space are modern, you're going to need to give the room a temporary face lift. If you're wondering what a kitchen from the 1950s might have looked like, Kitchen Decorating Idea offers tips on how to outfit your space. Dream Kitchen in the UK offers a bunch of Retro Kitchen Accessories. Once you know what your space should look like, you can raid your home, your family members' homes, and your friends' homes for accessories.
How far are you willing to go for a vintage photo shoot? Have you thought about appliances and kitchen accessories or just your clothes?